An aerial view of a town with a river, buildings, and surrounding greenery.

Apartments in Chestertown for Rent

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Chestertown apartments

Property grounds

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (118 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
$144 nightly
The price is $159
Aug 3 - Aug 4
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
TV, fireplace

Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
$270 nightly
The price is $280
Aug 5 - Aug 6
Total with taxes and fees
Secluded Cottage in Middle of Chestertown
Beach nearby

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (26 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
$343 nightly
The price is $379
Aug 30 - Aug 31
Total with taxes and fees
Waterfront Retreat with Private Dock and Beach
Beach

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (27 reviews)
"This is an excellent cute little bungalow close to the beautiful town of Rock Hall. My wife and I enjoyed this very clean and neat place to stay while we enjoyed visiting our family. The host keeps everything very well kept on this property for his visitors! Highly recommend!!"
United States
DEAN
$264 nightly
The price is $292
Aug 2 - Aug 3
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
WiFi, bed sheets

Turtle Cove Room

Turtle Cove Room
Kent County
$160 nightly
The price is $174
Aug 3 - Aug 4
Total with taxes and fees
Turtle Cove Room
Property grounds

Beachcomber Suite

Beachcomber Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...
United States
Lisa E.
$167 nightly
The price is $181
Aug 10 - Aug 11
Total with taxes and fees
Beachcomber Suite
Exterior

Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.8 out of 10, Exceptional, (23 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
$118 nightly
The price is $125
Aug 10 - Aug 11
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
Smart TV

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Havre de Grace
10.0 out of 10, Exceptional, (12 reviews)
"Very cool place, walking distance to everything."
United States
Brett S.
$255 nightly
The price is $270
Aug 24 - Aug 25
Total with taxes and fees
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Terrace/patio

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Aberdeen
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful location, nicely decorated. The host thought of everything you may need including a free snack basket, washer/dryer with detergent and dryer sheets, BBQ grill with utensils, board games and cards, kayaks and life vests, hot tub, firetable etc."
United States
Andy W.
$201 nightly
The price is $213
Aug 3 - Aug 4
Total with taxes and fees
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (86 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
$424 nightly
The price is $483
Aug 2 - Aug 3
Total with taxes and fees
Waterfront Oasis of Annapolis Star
Coffee/tea maker, fridge, microwave, oven

18th Cent. Charm in Historic Downtown Annapolis

18th Cent. Charm in Historic Downtown Annapolis
Historic District
9.0 out of 10, Wonderful, (14 reviews)
"Jen was an amazing host. The property was meticulously maintained. She made sure we had everything we needed! Shen created an environment where we could socialize with other guests or keep to ourselves. She made plenty of recommendations for local eateries and entertainment. We would definitely stay again!"
United States
Maureens B.
$355 nightly
The price is $405
Aug 4 - Aug 5
Total with taxes and fees
18th Cent. Charm in Historic Downtown Annapolis
Marina

Cozy Fells Point Gem / In The Heart of Fells Point

Cozy Fells Point Gem / In The Heart of Fells Point
Fells Point
9.8 out of 10, Exceptional, (208 reviews)
"Appreciated the privacy."
United States
Marie
$192 nightly
The price is $222
Aug 3 - Aug 4
Total with taxes and fees
Cozy Fells Point Gem / In The Heart of Fells Point
Coffee/tea maker, fridge, microwave, oven

Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (5 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
$417 nightly
The price is $475
Aug 1 - Aug 2
Total with taxes and fees
Pool Loft Suite | Bay Access & Beach Passes
Interior

Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC

Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Greektown
9.8 out of 10, Exceptional, (14 reviews)
"The house was clean and the beds were comfortable. "
United States
Karen B.
$228 nightly
The price is $263
Aug 5 - Aug 6
Total with taxes and fees
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
1 bedroom, in-room safe, desk, iron/ironing board

Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals

Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
Nottingham City
$134 nightly
The price is $155
Aug 3 - Aug 4
Total with taxes and fees
Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
Living area

Home away from home with WiFi and AC in delightful Parkville

Home away from home with WiFi and AC in delightful Parkville
Carney
$191 nightly
The price is $221
Aug 23 - Aug 24
Total with taxes and fees
Home away from home with WiFi and AC in delightful Parkville
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chestertown Hotel Reviews

Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent
"Won’t stay again. No Breakfast and no grill"
PINKS 1-night trip
Posted 6 hours ago
Hilton Garden Inn Baltimore/White Marsh

Find out more about Chestertown

Chestertown Apartments information

Number of reviews
539
Accommodation
79 Apartments
Lowest Price
$125
Highest Price
$483

Frequently asked questions

What's it like to stay at an apartment in Chestertown?
You can choose from 5 apartments in Chestertown for your vacation.
Why should you consider apartments instead of traditional hotels?
An apartment comes equipped with a kitchen, so you can cook some of your meals, and usually is more spacious than a traditional hotel room. Apartments are a good option for solo travelers who want to live like locals, and also for families wanting the conveniences of home.
What's the top apartment for my stay in Chestertown?
First Floor Studio Apartment in Historic Chestertown: Includes a private pool, free WiFi, and private patios. A fitness center and onsite laundry facilities are on site. Historic Downtown Garden Oasis with Private Patio: Free WiFi, outdoor space, and separate dining areas are included.
How many apartments can I expect to find in Chestertown?
Expedia has 5 apartments to book in Chestertown.
What can I expect from the weather during my trip to Chestertown?
Weather is only one factor, but it can really affect your travel plans, especially when you're planning an extended stay in Chestertown. The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
What should I see and do in Chestertown?
Cultural attractions include Garfield Center for the Arts at the Prince Theater and Historical Society of Kent County Maryland, whereas Northern Chesapeake Bay and Chesapeake Bay are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Chestertown Historic District and Rolphs Wharf Marina.
What's the best way to get to and around Chestertown?
Knowing a bit about the transportation options can make your trip smoother when you get to your destination. Fly into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) from the heart of the city. Otherwise, you can search for flights to Easton, MD (ESN-Easton - Newnam), which is 28.2 mi (45.3 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.

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